GB757045A - Benzo(h)quinolin-ols as azine cyan colour formers for colour photography - Google Patents

Benzo(h)quinolin-ols as azine cyan colour formers for colour photography

Info

Publication number
GB757045A
GB757045A GB5306/54A GB530654A GB757045A GB 757045 A GB757045 A GB 757045A GB 5306/54 A GB5306/54 A GB 5306/54A GB 530654 A GB530654 A GB 530654A GB 757045 A GB757045 A GB 757045A
Authority
GB
United Kingdom
Prior art keywords
quinoline
sulphonic acid
prepared
aminobenzo
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB5306/54A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
GAF Chemicals Corp
Original Assignee
General Aniline and Film Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by General Aniline and Film Corp filed Critical General Aniline and Film Corp
Publication of GB757045A publication Critical patent/GB757045A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/10—Aza-phenanthrenes
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/32—Colour coupling substances
    • G03C7/3244—Couplers forming azinic dyes; Specific developers therefor

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Quinoline Compounds (AREA)

Abstract

Benzo-(h)-quinoline-5-ol is prepared by heating together 4-amino-2-naphthalenesulphonic acid, glycerol, concentrated sulphuric acid, and picric acid, and fusing the product with sodium hydroxide. Benzo-(h)-quinoline-6-ol is similarly prepared. Benzo-(h)-quinoline-6 : 9-diol is prepared by fusing benzo-(h)-quinoline-6 : 9-disulphonic acid with potassium hydroxide and sodium hydroxide. Benzo-(h)-quinoline-5 : 9-diol is similarly prepared. Benzo-(h)-quinoline-6 : 9-disulphonic acid is prepared by heating together 4-aminonaphthalene - 1 : 6 - disulphonic acid, glycerol, concentrated sulphuric acid, and picric acid. 9 - Hydroxybenzo - (h) - quinoline - 5 - sulphonic acid and -6-sulphonic acid are similarly prepared. 4 - Aminonaphthalene - 1 : 6 - disulphonic acid is obtained by dissolving Dahl's acid (a crude mixture of 4-aminonaphthalene-1 : 6- and -1 : 7-disulphonic acids) in hot water with the aid of sodium acetate, and treating the filtered solution with a large excess of acetic acid and crystallizing. The crystalline cake obtained is dissolved in hot water containing ammonium hydroxide to make a neutral solution and is saturated with calcium chloride and the calcium salt crystallized. The calcium salt is converted to the potassium salt and the solution of the latter obtained is acidified with excess acetic acid and allowed to crystallize. 9 - Aminobenzo - (h) - quinoline - 6 - ol is prepared by heating potassium 9-aminobenzo-(h)-quinoline-6-sulphonate with potassium hydroxide solution in an autoclave, filtering, acidifying, and finally salting out with anhydrous sodium sulphate. Potassium 9 - aminobenzo - (h) - quinoline-6-sulphonate is prepared by heating in an autoclave a mixture of 9-hydroxybenzo-(h)-quinoline-6-sulphonic acid, aqueous ammonium hydroxide, and aqueous sulphur dioxide, and finally precipitating with potassium chloride. 9 - Acetylaminobenzo - (h) - quinoline - 6 - ol is prepared by acetylating 9-aminobenzo-(h)-quinoline-6-ol using excess of acetic anhydride in the presence of aqueous sodium carbonate. 9 - Acetylaminobenzo - (h) - quinoline - 6 - ol-A-sulphonic acid is similarly prepared. 9 - Aminobenzo - (h) - quinoline - 6 - ol - X-sulphonic acid is prepared by sulphonating 9-aminobenzo-(h)-quinoline-6-ol hydrochloride. 9 - p - Toluenesulphonylaminobenzo - (h)-quinoline - 6 - ol - X - sulphonic acid is prepared by reacting 9-aminobenzo-(h)-quinoline-6-ol-X-sulphonic acid in hot sodium acetate solution with p-toluenesulphonyl chloride. 9 - Octadecylsulphonylaminobenzo - (h) - quinoline-6-ol-X-sulphonic acid is prepared by adding a pyridine solution of octadecylsulphonyl chloride dropwise to a pyridine solution of 9-aminobenzo - (h) - quinoline - 6 - ol - X - sulphonic acid and refluxing. 9-Tetradecylsulphonylbenzo - (h) - quinoline - 6 - ol - X - sulphonic acid and 9-(31-nitrobenzenesulphonyl)-aminobenzo - (h) - quinoline - 6 - ol - X - sulphonic acid are similarly prepared. 9 - (31 - Aminobenzenesulphonyl) - aminobenzo - (h) - quinoline - 6 - ol - X - sulphonic acid is prepared by reducing 9-(31-nitrobene-sulphonyl) - aminobenzo - (h) - quinoline - 6-ol-X-sulphonic acid with an aqueous solution of sodium hydrosulphite and sodium hydroxide. 9 - (31 - Tetradecanoylaminobenzenesulphonyl)-aminobenzo - (h) - quinoline - 6 - ol - X - sulphonic acid is prepared by adding a benzene solution of myristoyl chloride dropwise to a benzene-pyridine pyridine solution of 9-(31-aminobenzenesulphonyl) - aminobenzo - (h)-quinoline-6-ol-X-sulphonic acid. 9 - (71 - Carboxy - 21 - naphthyl) - aminobenzo - (h) - quinoline - 6 - ol - X - sulphonic acid is prepared by refluxing together a mixture of water, sodium hydroxide, 7-hydroxy-2-naphthoic acid, 9 - aminobenzo - (h) - quinoline - 6-ol-X-sulphonic acid, and sodium metabisulphite. 9 - 21 - [71 - (111 - Octadecyl - 511 - sulpho - 211-benzimidazolyl) - phenylcarbamyl] - naphthylaminobenzo - (h) - quinoline - 6 - ol - X - sulphonic acid is prepared by refluxing together pyridine, benzene, 9 - (71 - carboxynaphthyl)-aminobenzo - (h) - quinoline - 6 - ol - X - sulphonic acid, and 1-octadecyl-2-(41-aminophenyl) - benzimidazole - 5 - sulphonic acid, removing part of the mixed solvent by distillation, and adding a benzene solution of phosphorus trichloride. 9 - 21 - [71 - (111 - Methyl - 611-myristoylamino - 411 - sulpho) - phenylcarbamyl]-naphthylaminobenzo - (h) - quinoline - 6 - ol - X-sulphonic acid is similarly prepared. 9 - Methylaminobenzo - (h) - quinoline - 6 - ol is prepared by heating together in an autoclave a mixture of benzo-(h)-quinoline-9-ol-6-sulphonic acid, aqueous methylamine solution, and saturated sulphur dioxide solution to obtain 9 - methylaminobenzo - (h) - quinoline-6-sulphonic acid, and heating the latter in an autoclave with aqueous potassium hydroxide. 7 - Carboxybenzo - (h) - quinoline - 6 - ol is prepared by heating together 7-cyanobenzo-(h)-quinoline-6-sulphonic acid and aqueous potassium hydroxide in an autoclave and acidifying. 7 - Cyanobenzo - (h) - quinoline - 6 - sulphonic acid is prepared by diazotizing acidified 7-aminobenzo - (h) - quinoline - 6 - sulphonic acid, adding the diazonium salt to an aqueous solution of cuprous cyanide and sodium cyanide, salting out, and purifying. 7 - Aminobenzo - (h) - quinoline - 6 - sulphonic acid is prepared by reducing with iron and acetic acid 7-nitrobenzo-(h)-quinoline-6-sulphonic acid, itself prepared by nitrating benzo-(h)-quinoline-6-sulphonic acid with nitric and sulphuric acids. 9 - [21 - (41:61 - dimethylamino - 1:3:5-triazinylamino)] - benzo - (h) - quinoline - 6 - ol-X-sulphonic acid is prepared by reacting 9-aminobenzo - (h) - quinoline - 6 - ol - X - sulphonic acid with cyanuric chloride in presence of aqueous potassium hydroxide, and then heating with aqueous methylamine solution. 6 - Aminobenzo - (h) - quinoline - 9 - ol and 6:9 - diaminobenzo - (h) - quinoline are prepared by heating together benzo-(h)-quinoline-6:9-diol, concentrated ammonium hydroxide, and aqueous sulphur dioxide in an autoclave, and are separated. 6 - p - Toluenesulphonamidobenzo - (h) - quinoline-9-ol is prepared by refluxing together 6-aminobenzo - (h) - quinoline - 9 - ol hydrochloride, pyridine, and benzene, adding p-toluenesulphonyl chloride dissolved in benzene, and heating. 9 - (81 - Carboxymethoxy - 2 - naphthylamino)-benzo - (h) - quinoline - 6 - ol - X - sulphonic acid is prepared by refluxing together the sodium salts of 8-carboxymethoxy-2-naphthylamine and 6 - hydroxy - 9 - aminobenzo - (h) - quinoline-X-sulphonic acid in aqueous sodium bisulphite solution. 9 - Methanesulphonamidobenzo - (h) - quinoline-6-ol-X-sulphonic acid is prepared by reacting 9 - aminobenzo - (h) - quinoline - 6 - ol-X-sulphonic acid in pyridine or aqueous alkaline solution with methanesulphonyl chloride. 6 - Methanesulphonamidobenzo - (h) - quinoline - 9 - ol, 9 - p - toluenesulphon - N - methylamidobenzo - (h) - quinoline - 6 - ol, and 6 - p-toluenesulphonamidobenzo - (h) - quinoline - 9 - ol are similarly prepared, 9 - Methanesulphonamido - 6 - aminobenzo-(h)-quinoline is prepared by heating with ammonium hydroxide solution and sodium bisulphite solution in an autoclave 9-methanesulphonamidobenzo - (h) - quinoline - 6 - ol, itself obtained by reacting 9-aminobenzo-(h)-quinoline-6-ol with methanesulphonyl chloride in pyridine solution. 10 - Aminobenzo - (h) - quinoline - 6 - ol is prepared by heating with potassium hydroxide in an autoclave 10-aminobenzo-(h)-quinoline-6-sulphonic acid, itself prepared by reducing with iron and water 10-nitrobenzo-(h)-quinoline-6-sulphonic acid. The latter is separated as the more insoluble sodium salt from a mixture with 7 - nitrobenzo - (h) - quinoline - 6 - sulphonic acid obtained by nitrating with fuming nitric acid in cold concentrated sulphuric acid benzo-(h)-quinoline-6-sulphonic acid, obtained by the Skraup reaction from 1-aminonaphthalene-4-sulphonic acid. Specifications 644,863 and 649,811 are referred to.
GB5306/54A 1953-02-24 1954-02-23 Benzo(h)quinolin-ols as azine cyan colour formers for colour photography Expired GB757045A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US338396A US2717831A (en) 1953-02-24 1953-02-24 Benzo(h)quinolin-ols as azine cyan color formers

Publications (1)

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GB757045A true GB757045A (en) 1956-09-12

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Family Applications (1)

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GB5306/54A Expired GB757045A (en) 1953-02-24 1954-02-23 Benzo(h)quinolin-ols as azine cyan colour formers for colour photography

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US (1) US2717831A (en)
BE (1) BE526742A (en)
DE (1) DE958527C (en)
FR (1) FR1095992A (en)
GB (1) GB757045A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4521423A (en) * 1983-10-31 1985-06-04 Ayerst, Mckenna & Harrison, Ltd. 7,8,9,10-Tetrahydrobenzo[h]quinolin-9-amine derivatives and compositions and methods for treating depression employing them
US5260177A (en) * 1988-03-16 1993-11-09 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US4990436A (en) * 1990-01-23 1991-02-05 Eastman Kodak Company Cyan dye-forming couplers and photographic recording materials containing same

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2486440A (en) * 1946-01-10 1949-11-01 Gen Aniline & Film Corp Production of phenazonium dyestuff images

Also Published As

Publication number Publication date
BE526742A (en)
DE958527C (en) 1957-02-21
US2717831A (en) 1955-09-13
FR1095992A (en) 1955-06-08

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